IE920943A1 - New heterocycle-substituted alkylamides, process for¹preparing them and pharmaceutical compositions containing¹them - Google Patents
New heterocycle-substituted alkylamides, process for¹preparing them and pharmaceutical compositions containing¹themInfo
- Publication number
- IE920943A1 IE920943A1 IE094392A IE920943A IE920943A1 IE 920943 A1 IE920943 A1 IE 920943A1 IE 094392 A IE094392 A IE 094392A IE 920943 A IE920943 A IE 920943A IE 920943 A1 IE920943 A1 IE 920943A1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- compound
- ethyl
- group
- lower alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 48
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 127
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- -1 alkali metal salt Chemical class 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 239000002585 base Substances 0.000 claims description 16
- 238000004587 chromatography analysis Methods 0.000 claims description 16
- 238000002425 crystallisation Methods 0.000 claims description 16
- 230000008025 crystallization Effects 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000007796 conventional method Methods 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 230000009471 action Effects 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 206010022437 insomnia Diseases 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 230000002490 cerebral effect Effects 0.000 claims description 3
- 230000004087 circulation Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 2
- 208000000044 Amnesia Diseases 0.000 claims description 2
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- LLTLVNMMLFQGLO-UHFFFAOYSA-N O=C1CC=C2N(C)C(CCNC(C)=O)OC2=C1 Chemical compound O=C1CC=C2N(C)C(CCNC(C)=O)OC2=C1 LLTLVNMMLFQGLO-UHFFFAOYSA-N 0.000 claims description 2
- 206010033664 Panic attack Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 208000028017 Psychotic disease Diseases 0.000 claims description 2
- 206010039792 Seborrhoea Diseases 0.000 claims description 2
- 206010039966 Senile dementia Diseases 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 206010000496 acne Diseases 0.000 claims description 2
- 230000032683 aging Effects 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 235000021229 appetite regulation Nutrition 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 206010016256 fatigue Diseases 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 2
- 208000024714 major depressive disease Diseases 0.000 claims description 2
- 201000003995 melancholia Diseases 0.000 claims description 2
- 230000006984 memory degeneration Effects 0.000 claims description 2
- 208000023060 memory loss Diseases 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 208000019906 panic disease Diseases 0.000 claims description 2
- 230000001575 pathological effect Effects 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 208000012672 seasonal affective disease Diseases 0.000 claims description 2
- 208000008742 seborrheic dermatitis Diseases 0.000 claims description 2
- 230000035882 stress Effects 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000003433 contraceptive agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 abstract description 2
- 229940126601 medicinal product Drugs 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 187
- 239000000047 product Substances 0.000 description 54
- 238000004566 IR spectroscopy Methods 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 24
- 239000012346 acetyl chloride Substances 0.000 description 24
- 101150041968 CDC13 gene Proteins 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 21
- MKMCJLMBVKHUMS-UHFFFAOYSA-N Coixol Chemical compound COC1=CC=C2NC(=O)OC2=C1 MKMCJLMBVKHUMS-UHFFFAOYSA-N 0.000 description 20
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 16
- 241001465754 Metazoa Species 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 150000001408 amides Chemical class 0.000 description 15
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 15
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
- 238000000921 elemental analysis Methods 0.000 description 12
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 12
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 10
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 9
- 150000003857 carboxamides Chemical class 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 238000003760 magnetic stirring Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- BSEXNZMHLUMQKR-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1.NC(=O)C1CC1 BSEXNZMHLUMQKR-UHFFFAOYSA-N 0.000 description 6
- 229940047889 isobutyramide Drugs 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 102000001419 Melatonin receptor Human genes 0.000 description 5
- 108050009605 Melatonin receptor Proteins 0.000 description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 230000000302 ischemic effect Effects 0.000 description 5
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 description 5
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 229950001902 dimevamide Drugs 0.000 description 4
- 230000012173 estrus Effects 0.000 description 4
- 229960003987 melatonin Drugs 0.000 description 4
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 230000000949 anxiolytic effect Effects 0.000 description 3
- NXWBOAQGGZVKBT-UHFFFAOYSA-N cyclobutanecarboxamide Chemical compound NC(=O)C1C[CH]C1 NXWBOAQGGZVKBT-UHFFFAOYSA-N 0.000 description 3
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000004089 microcirculation Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 210000003101 oviduct Anatomy 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- BXQNSPXDWSNUKE-UHFFFAOYSA-N 1,3-benzothiazole 1-oxide Chemical compound C1=CC=C2S(=O)C=NC2=C1 BXQNSPXDWSNUKE-UHFFFAOYSA-N 0.000 description 2
- QLXOYBMXNAQZAG-UHFFFAOYSA-N 2-(2-aminoethyl)-3-methyl-2,5-dihydro-1,3-benzothiazol-6-one;hydrochloride Chemical compound Cl.O=C1CC=C2N(C)C(CCN)SC2=C1 QLXOYBMXNAQZAG-UHFFFAOYSA-N 0.000 description 2
- BOJPNZPJXWLSPD-UHFFFAOYSA-N 2-(2-aminoethyl)-3-methyl-2,5-dihydro-1,3-benzoxazol-6-one;hydrochloride Chemical compound Cl.O=C1CC=C2N(C)C(CCN)OC2=C1 BOJPNZPJXWLSPD-UHFFFAOYSA-N 0.000 description 2
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 2
- IRRLPKMHOQFNPW-UHFFFAOYSA-N 3-(2-aminoethyl)-6-methoxy-1,3-benzoxazol-2-one Chemical compound COC1=CC=C2N(CCN)C(=O)OC2=C1 IRRLPKMHOQFNPW-UHFFFAOYSA-N 0.000 description 2
- QRMRRLXXFHXMBC-UHFFFAOYSA-N 3-methyl-1,3-benzoxazol-2-one Chemical compound C1=CC=C2OC(=O)N(C)C2=C1 QRMRRLXXFHXMBC-UHFFFAOYSA-N 0.000 description 2
- CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 2
- FRCSCYPTWREXJE-UHFFFAOYSA-N 5-methoxy-1,3-benzothiazole 1-oxide Chemical compound COC=1C=CC2=C(N=CS2=O)C=1 FRCSCYPTWREXJE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- RHJVIGLEIFVHIJ-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1[CH]CCCC1 RHJVIGLEIFVHIJ-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- DPMYDKMPEGCNCP-UHFFFAOYSA-N n-[2-(7-methoxy-4-oxo-1,2-benzoxazin-3-yl)ethyl]acetamide Chemical compound O1N=C(CCNC(C)=O)C(=O)C=2C1=CC(OC)=CC=2 DPMYDKMPEGCNCP-UHFFFAOYSA-N 0.000 description 2
- 230000016087 ovulation Effects 0.000 description 2
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- 238000004611 spectroscopical analysis Methods 0.000 description 2
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- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical class CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
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- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9103538A FR2674524B1 (fr) | 1991-03-25 | 1991-03-25 | Nouveaux amides alkyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IE920943A1 true IE920943A1 (en) | 1992-10-07 |
Family
ID=9411046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE094392A IE920943A1 (en) | 1991-03-25 | 1992-03-25 | New heterocycle-substituted alkylamides, process for¹preparing them and pharmaceutical compositions containing¹them |
Country Status (13)
| Country | Link |
|---|---|
| US (7) | US5240919A (fr) |
| EP (1) | EP0506539B1 (fr) |
| JP (1) | JPH0794448B2 (fr) |
| AT (1) | ATE152448T1 (fr) |
| AU (1) | AU649115B2 (fr) |
| CA (1) | CA2063885A1 (fr) |
| DE (1) | DE69219394T2 (fr) |
| DK (1) | DK0506539T3 (fr) |
| ES (1) | ES2102475T3 (fr) |
| FR (1) | FR2674524B1 (fr) |
| GR (1) | GR3023936T3 (fr) |
| IE (1) | IE920943A1 (fr) |
| NZ (1) | NZ242104A (fr) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2674524B1 (fr) * | 1991-03-25 | 1993-05-21 | Adir | Nouveaux amides alkyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2702214B1 (fr) * | 1993-03-05 | 1995-04-14 | Adir | Nouveaux composés (aryl(alkyl)carbonyl)-hétérocycliques, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent. |
| US5506268A (en) * | 1993-06-11 | 1996-04-09 | Nps Pharmaceuticals, Inc. | Use of isovaleramide as a mild anxiolytic and sedative agent |
| FR2717810B1 (fr) * | 1994-03-22 | 1996-04-26 | Adir | Nouvelles aminoalkyl benzoxazolinones et benzothiazolinones, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| AU2109695A (en) | 1994-03-30 | 1995-10-23 | Novartis Ag | Screening method using the rzr receptor family |
| US5856124A (en) | 1994-06-17 | 1999-01-05 | The General Hospital Corporation | DNA encoding high-affinity melatonin receptors |
| US7081349B1 (en) | 1994-06-17 | 2006-07-25 | The General Hospital Corporation | High-affinity melatonin receptor and uses thereof |
| US5496826A (en) * | 1994-09-02 | 1996-03-05 | Bristol-Myers Squibb Company | Pharmaceutical methods of using heterocyclic derivatives of N-phenylamides |
| US5541228A (en) * | 1994-10-14 | 1996-07-30 | Bristol-Myers Squibb Co. | Melatonergic agents |
| US5530012A (en) | 1994-12-22 | 1996-06-25 | Bristol-Myers Squibb Co. | 3-alkoxybenzylpiperidine derivatives as melatonergic agents |
| US5661186A (en) * | 1995-02-24 | 1997-08-26 | Bristol-Myers Squibb Co. | Tetralinyl-and indanyl-ethylamides |
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| CA928296A (en) * | 1967-06-05 | 1973-06-12 | Umio Suminori | N-substituted and n, n-disubstituted aminocarbonylalkyl compounds and their production |
| CH532077A (de) * | 1968-05-31 | 1972-12-31 | Robapharm A G | Verfahren zur Herstellung von neuen basischen Derivaten des Benzoxazolin-2-ons |
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| FR2646350B1 (fr) * | 1989-04-28 | 1991-06-28 | Adir | Nouveaux derives benzothiazolinoniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US5166353A (en) * | 1989-04-28 | 1992-11-24 | Adir Et Compagnie | Benzothiazolinone compounds |
| US5260297A (en) * | 1989-07-13 | 1993-11-09 | Rhone Poulenc Rorer, S.A. | 2-imino-3-alkylbenzothiazoline derivatives bearing a heterocyclic substituent on the alkyl group, their preparation and medicinal products containing them. |
| JPH0678327B2 (ja) * | 1989-07-20 | 1994-10-05 | ファイザー製薬株式会社 | ４，５，６，７，―四置換ベンゾオキサゾロン類 |
| FR2655042B1 (fr) * | 1989-11-29 | 1994-01-21 | Adir Cie | Nouvelles benzothiazolinones substituees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2658823B1 (fr) * | 1990-02-27 | 1992-04-30 | Adir | Nouveaux derives d'aminomethylpiperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent . |
| FR2663634B1 (fr) * | 1990-06-22 | 1992-09-04 | Adir | Nouvelles acyl benzoxazolinones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5268381A (en) * | 1990-09-26 | 1993-12-07 | Adir Et Compagnie | Aminoalkyl-benzothiazolinone and -benzoxazolinone compounds having a high 5-HT1A affinity |
| FR2667068B1 (fr) * | 1990-09-26 | 1994-09-09 | Adir | Nouvelles amines alkyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5234924A (en) * | 1990-09-26 | 1993-08-10 | Adir Et Compagnie | Benzothiazine and benzothiazole compounds useful as analgesics |
| FR2674524B1 (fr) * | 1991-03-25 | 1993-05-21 | Adir | Nouveaux amides alkyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
-
1991
- 1991-03-25 FR FR9103538A patent/FR2674524B1/fr not_active Expired - Fee Related
-
1992
- 1992-03-09 US US07/848,373 patent/US5240919A/en not_active Expired - Fee Related
- 1992-03-24 CA CA002063885A patent/CA2063885A1/fr not_active Abandoned
- 1992-03-24 DK DK92400782.6T patent/DK0506539T3/da active
- 1992-03-24 NZ NZ242104A patent/NZ242104A/xx unknown
- 1992-03-24 AU AU13112/92A patent/AU649115B2/en not_active Ceased
- 1992-03-24 AT AT92400782T patent/ATE152448T1/de not_active IP Right Cessation
- 1992-03-24 ES ES92400782T patent/ES2102475T3/es not_active Expired - Lifetime
- 1992-03-24 DE DE69219394T patent/DE69219394T2/de not_active Expired - Fee Related
- 1992-03-24 EP EP92400782A patent/EP0506539B1/fr not_active Expired - Lifetime
- 1992-03-25 IE IE094392A patent/IE920943A1/en not_active Application Discontinuation
- 1992-03-25 JP JP4067453A patent/JPH0794448B2/ja not_active Expired - Lifetime
-
1993
- 1993-04-28 US US08/054,720 patent/US5322843A/en not_active Expired - Fee Related
- 1993-04-28 US US08/054,604 patent/US5326775A/en not_active Expired - Fee Related
- 1993-04-28 US US08/055,665 patent/US5300507A/en not_active Expired - Fee Related
- 1993-04-28 US US08/054,596 patent/US5322849A/en not_active Expired - Fee Related
- 1993-06-15 US US08/078,001 patent/US5386034A/en not_active Expired - Fee Related
-
1994
- 1994-04-05 US US08/223,176 patent/US5436348A/en not_active Expired - Fee Related
-
1997
- 1997-06-30 GR GR970401584T patent/GR3023936T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ242104A (en) | 1994-09-27 |
| DE69219394D1 (de) | 1997-06-05 |
| JPH0794448B2 (ja) | 1995-10-11 |
| EP0506539B1 (fr) | 1997-05-02 |
| CA2063885A1 (fr) | 1992-09-26 |
| FR2674524B1 (fr) | 1993-05-21 |
| ATE152448T1 (de) | 1997-05-15 |
| DE69219394T2 (de) | 1997-12-11 |
| EP0506539A1 (fr) | 1992-09-30 |
| US5240919A (en) | 1993-08-31 |
| ES2102475T3 (es) | 1997-08-01 |
| FR2674524A1 (fr) | 1992-10-02 |
| GR3023936T3 (en) | 1997-09-30 |
| US5326775A (en) | 1994-07-05 |
| US5322849A (en) | 1994-06-21 |
| AU1311292A (en) | 1992-10-01 |
| US5386034A (en) | 1995-01-31 |
| US5300507A (en) | 1994-04-05 |
| JPH0597828A (ja) | 1993-04-20 |
| AU649115B2 (en) | 1994-05-12 |
| US5436348A (en) | 1995-07-25 |
| US5322843A (en) | 1994-06-21 |
| DK0506539T3 (da) | 1997-12-01 |
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| Date | Code | Title | Description |
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| FJ9A | Application deemed to be withdrawn section 31(3) |